


Yes, Sir

by SoraJinsei



Series: NSFW [2]
Category: Supernatural
Genre: Bisexual Dean Winchester, Bottom Castiel/Top Dean Winchester, Butler Castiel (Supernatural), Butt Plugs, Castiel Loves Dean Winchester, Castiel is a Tease, Castiel/Dean Winchester Mutual Pining, Edgeplay, M/M, Mutual Pining, NSFW, One Shot, Porn With Plot, Power Bottom Castiel (Supernatural), Rich Dean Winchester, Smut, Suits, Teasing, Tied-Up Dean Winchester, Top Dean Winchester
Language: English
Status: Completed
Published: 2019-11-22
Updated: 2019-11-22
Packaged: 2021-02-25 23:21:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,920
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21523636
Author URL: https://archiveofourown.org/users/SoraJinsei/pseuds/SoraJinsei
Summary: As a loyal servant to the richest family in the world, Castiel never thought his boss would have eyes for him.
Relationships: Castiel/Dean Winchester
Series: NSFW [2]
Series URL: https://archiveofourown.org/series/1548268
Comments: 11
Kudos: 201





	Yes, Sir

  
  
  
  
  
Castiel grew up in this lifestyle. Rather be in embarrassed, he takes pride.  
  
His father and mother were both servants.  
  
He got the best education until he was pulled out at fifteen, homeschooled, and graduating the following year.  
  
Castiel could have become a doctor, a lawyer, heck, even the president with how smart he was, but he decided to stay humble, if you will, by becoming a servant to one of the richest families in the world.  
  
The Winchesters.  
  
They pay their staff handsomely, full medical benefits, days off whenever you need, you name it.  
  
This is where he finds himself now, watching the servants around him finish their last-minute touch-ups to make sure the mansion was up to par before Mr. Winchester came home. The house was immaculate already, but knowing the Master of the house was coming back, there was no room for error.  
  
As the Butler and personal confidant to the billionaire, Castiel did have his own standards to uphold.  
  
He was taught by his parents from a young age that he would take over as a personal servant to the Winchester family once they were able to retire.  
  
By his 25th birthday, Dean Winchester, the oldest son of John and Mary, had inherited the fortune after his parents were killed in a car accident.  
  
Around the same time, Castiel's parents had retired.  
  
Mr. Winchester had inherited one of the world's largest oil companies in the world.  
  
But alas, having all this money and anything he wanted, one thing is for sure, a man can get lonely.  
  
That being said, Castiel had witnessed the comings and goings over the years of all Mr. Winchesters exploits as they attempted to leave in the mornings. Castiel not saying a word but being kind enough to extend them breakfast as a courtesy  
  
Lately, he's noticed, Mr. Winchester acting quite strange.

One night he had brought one of his latest conquests, a supermodel, home from some big charity event.  
  
The next night, he brought a man home.  
  
Like a good servant, he doesn't say anything. He still brings Dean his coffee in the morning and lays out his outfits in the morning.  
  
But that sense of normalcy escalates again one night, a night Dean decided to stay home, alone.  
  
Castiel had just placed the dinner plate in front of the man, intending to grab the napkin to place it on his lap when a grip on his wrist stopped him.  
  
"Sir?" Castiel questioned, gazing down at the man. Dean had his eyes downcast, his free hand sitting on the table in a clenched fist. Castiel watched as Dean pushed the food away.  
  
He was about to call for his attention again but was silenced by the sudden scraping of a chair against the tile.  
  
Dean rose from his seat, letting go of Castiel's wrist in the process and turning towards his trusted servant. Those green eyes looking anywhere but at the man before him.  
  
"Sir?" Castiel asked again.  
  
“Now or Never” Castiel could swear he heard the man whisper before hands were cupping either side of Castiel's neck.  
  
Dean glanced into the man's eyes briefly before leaning in to kiss him.  
  
He was being kissed.  
  
He. Was. Being. Kissed.  
  
By his boss.  
  
Bringing two hands up, Castiel placing them firmly on Mr. Winchester’s chest, giving a hard push until their lips separated and Dean was staring at him in shock.  
  
The kiss hadn’t lasted that long...so why was Castiel’s heart racing like crazy?  
  
“C-Cas...I’m sorry-” he was silenced when Castiel raised a hand to silence him. Taking deep breaths to calm himself. Looking around the room, his eyes settling on the two servants standing by the kitchen door on the other side of the room, down a ways from them. Seemingly unaware of what was going on, their gazes unwavering as they stared into space. Acting like they were not even there. As they were trained to be.  
  
“Out!” Castiel commanded, watching them jump at the tone before making their way through the kitchen door.  
  
Dean watched them go, mouth tightly shut, unsure of what to do.  
  
Castiel let his eyes fall to the floor as he tried to smother a feeling he’s been squashing down for years.  
  
A feeling that spurred when he first laid eyes on the man before him.  
  
Yes, Castiel may have been a few years older, but this rich, spoiled, billionaire is all Castiel could think about while he was learning to take his father’s place. But when the time came, he buried those feelings down deep.  
  
For a man of Dean’s tastes and lifestyle, as Castiel took in the black suit, black-tie with red laced stripes with matching cufflinks, handkerchief, and a white button-up shirt. An outfit Castiel had picked out this morning due to the business meetings he was going to have...and...not because Castiel thought it would make the man look ridiculously good.  
  
Castiel did not fit in with Mr. Winchester’s criteria.  
  
“I can not return your...gesture,”  
  
“Gesture?” Dean started with a huff of laughter. A pang of something went straight to Castiel’s heart at that. “If you’re talking about you’re status-”  
  
“Of course I am.” Castiel cut off. “If one of those servants hadn’t signed a full disclosure agreement when they started working for you and had seen what you just did, they wouldn’t think twice to sell the story to the highest bidder,”  
  
Dean brought a hand to his chin, scratching it as he contemplated his next words.  
  
“So firing them is out of the question,” was all he said in such a nonchalant manner, causing blue eyes to roll in agitation.  
  
“That’s not the point here, Mr. Winchester-”  
  
“Dean,” Castiel stopped mid-sentence to widen his eyes. “Call me Dean. I’ve told you this before.” A warm feeling ignited somewhere below his stomach, his heart to flutter.  
  
“I c-can’t do that. I’m you’re employee-”  
  
“And you’ve been my friend since I was able to walk and talk,” Balling his hands into fists, Castiel closed his eyes, wishing it was enough to block out whatever else Dean was going to say.  
  
“And I honestly don’t care what people would think.” Hearing the man’s clothes shuffling a bit. Must be straightening his suit or something, Castiel told himself. “Since I was a kid, I admired you. That was until I realized it wasn’t admiration. I, uh, really like you.”  
  
This wasn’t real. It had to be a dream. In those nights where Castiel couldn’t sleep, the nights those green eyes haunting him, as his hands would slip under the band of his underwear. Imagining the man and things he would do to Dean. Kissing, biting, sucking.  
  
A hand on his neck snapped Castiel from his thoughts, opening his eyes to see just how close Mr. Winche-Dean had gotten. Enough to where Castiel could close the small gap between them, to make this dream a reality.  
  
“And from what I can tell...you feel the same,” Castiel had to hold back the gasp when the palm of Dean’s hand found itself on his groin. Not realizing he’d let the thoughts of those dreams affect him. “Please,” Dean whispered, his hand moving slightly, rubbing along the growing length.  
  
Castiel heard and felt the unbuckling of his belt, the zipper being pulled down, hissing when the warm hand pressed against his dick through the material of his underwear. He felt Dean’s face move closer, the smooth skin of his shaved chin touching his cheek. The cologne he was wearing sending shudders through Castiel’s body, his legs nearly collapsing when he felt a light kiss to his neck. One after another, covering Castiel’s entire neck as Dean’s hand continued to torment him through the cloth.  
  
Castiel was so lost in the feeling that he didn’t feel Dean’s hand on his neck move up until he felt the swipe of his thumb along Castiel’s bottom lip. A crazy thought appeared, blocking every warning bell ringing in his head as he decided to take that thumb into his mouth.  
  
Dean’s hand froze on Castiel’s crotch, blue eyes locking with green as he lapped at the digit, giving it a hard suck. Taking the momentary pause from the man, Castiel brought his hands up to curl them into the lapels of Dean’s suit, receiving a yelp in surprise when Castiel turned the man so that was pressed against the table.  
  
“Up,” Castiel's hands going straight for Dean’s belt and zipper. Shoving the pants and underwear down right as Dean hopped up to sit on the edge.  
  
Castiel took a second to admire the man before him.  
  
Unable to believe this was happening.  
  
The man staring at him with lust blown eyes, cheeks flushed, his suit rumpled from being manhandled, his cock fully erect and resting against said suit.  
  
“You’re bigger than I thought,” Castiel purred, taking in the sight before him.  
  
Leaning forward, Castiel took hold of the man’s cock, sweeping his tongue from the base to the tip, eliciting a low moan. Looking up through his eyelashes, he watched Dean tilt his head back and resting on his elbows, giving Castiel’s more room.  
  
He licked the tip with the flat part of his tongue, lapping up any precum that was leaking, all the while staring up at Dean who looked back with pure lust.  
  
Dean let out a sigh as Castiel took the tip into his mouth, slowly taking little by little until he was able to reach the base, hearing Dean let out a pant.  
  
Humming in response, which Castiel received a sharp gasp in return for, continued.  
  
“Cas-can’t-gonna-” Was all Castiel heard before letting go, a shuddering breath from Dean, but he didn’t cum.

Which is what Castiel was aiming for.  
  
Backing away, green eyes locking with blue.  
  
“Tell me what you want,” Castiel asked, his hand on his cock through the material, slowly stroking it as he kept the man’s gaze.  
  
“You,” was Dean’s response, his voice low, full of want as he watched the man before him in action.  
  
“Do you?” Castiel tutted, disbelief in his voice.  
  
“Yes,” feeling warmth spread throughout his body as Castiel nodded his head.  
  
“Then come get me,” and with that Castiel made a beeline for the door while hearing Dean’s shouts of protest.  
  
Castiel couldn't wipe the smile off his face as he wandered down the hall, hand tracing along the wall. Not caring that his pants are open for the world to see. Or staff.  
  
He slowed his pace when he saw the housekeeper, Meg, walking towards him, an arm full of towels while giving him a knowing look.  
  
"Playing games with your latest conquest again?" She asked, taking in his appearance. Smirking when she noticed his open front.  
  
"You could say that. Can you tell the rest of the staff that they can take the rest of the night off?"  
  
She gave a nod of her head, throwing in an overdramatic curtsey for good measure, making Castiel smile.  
  
"Have fun," she called over her shoulder as she walked away.  
  
He truly loved the girl, but after a one night stand, they realized they were just better off as friends. With a mutual booty call every now and then of course.  
  
Shaking his head, he continued down the hall, stopping once he got to his destination. He had his hand on the handle but was suddenly pushed up against the door, a body firmly pressing against him.  
  
"That was _very_ rude," the voice right in his ear. Castiel grinned over his shoulder at the assailant which only irritated the man more, pressing his body further onto Cas.  
  
Humming at the feel of Dean’s hard cock against the cleft of his ass. His hands roaming his body, finding themselves on Castiel's hips, gripping the materiel to pull them down, underwear included.  
  
"What the hell is this?" Came Dean's voice from Castiel's ass.  
  
"The obvious difference between your sexual experience and mine. I am always prepared." Castiel wiggled his ass before pushing it out more, giving Dean an eyeful. "No wonder all your male sexual partners left here limping,"  
  
He felt Dean tug at the plug experimentally.  
  
Castiel hummed, bringing his hips forward, out of Dean's grasp to turn around and gazing down at the man. One hand reaching behind him to turn the handle of the door.  
  
"If you'd like to know more…" Castiel trailed off as pushed the door open, stepping out of his pants, and walking back into the room, watching a very rumpled Mr. Winchester stare at him in awe.  
  
Pulling himself together, Dean stood up to follow, all the while roughly pulling his tie off, stripping his suit, and meeting Castiel in the middle of the room for a rough kiss.  
  
All teeth, biting, Dean's hand pulling the man as close as possible. Castiel moaning into the kiss as their cocks brushed against each other.  
  
Dean inched them both backward until Castiel's knees hit the bed, taking that opportunity to turn the man around, dropping to his knees.  
  
Castiel could feel the tug of the plug, sighing in relief when it was pulled out, but was short-lived when he felt the tip of Dean's tongue pushing past the wall of muscle.  
  
Hissing under his breath at the smack to his ass, moaning from the tongue, the only relief he got was when Dean pulled away, the feel of the head of his cock poking at his entrance less than a second later.  
  
"Fuck," Dean muttered, easily guiding himself all the way down to the base. He slowly pulled back before slamming back in.  
  
"I bet you're other partners couldn't have taken that so easily," Castiel mocked, looking over his shoulder with a smirk. He hissed in pain from the smack on his ass.  
  
"What? You don't like being proven wrong?" Another smack.  
  
"I'm going to take that as a-" Castiel instantly shut up when Dean pulled out and slamming back in, continuing the motion at a bruising pace. Giving Castiel's ass a good smack every now and then.  
  
Castiel's gripped the bed covers tightly, panting after each thrust.  
  
"H-hold on," Castiel managed to get out, one hand reaching back to stop the man from continuing. Dean gave one last thrust, keeping himself inside the man as he waited.  
  
"I have a better position than this,"  
  
"What the fuck?!" Dean grunted, irritated that he had to stop for that. "I was almost there!" He complained.  
  
Castiel took a deep breath, scooting onto the bed, feeling Dean's dick slip out.  
  
"Lay down here," patting the pillows right against the headboard.  
  
"Such a freaking cocktease," Dean grumbled out as he did as he was told. Meanwhile, Castiel grabbed Dean's tie, untying his own in the process.  
  
He kept his hands behind his back as he got on the bed, straddling the angry rich man who was leaning against the bedpost.  
  
Leaning down, he placed a kiss on those pouting lips, using the distraction to hold one of Dean's hands out to tie it to the bedpost.  
  
"H-hey!" Dean called out, trying to pull his arm free.  
  
"I told you, this a better position," taking the distraction to tie the other arm. "What? Has no one done this to you?” Castiel questioned. “Please tell me you haven’t been doing doggy style this entire time?”  
  
He was met with silence.  
  
“Don’t worry, I’ll show you so much more,” Castiel commented, sitting forward, reaching between his legs to grab hold of Dean’s angry red cock. Easing himself down, taking inch by inch, watching the man’s face contorting in pleasure until he reached the base, shuddering in delight at feeling so full.  
  
Castiel slowly starting rocking his hips, leaning back with a hand on the man’s chest.  
  
Dean let out a breathy moan at the sight before him, the expanse of skin, the muscles, mouth parted as he gasped and moaned as he continued rocking his hips faster and faster.  
  
"G-gonna-Cas-fuck!"  
  
Castiel couldn't help but smile down at the man after lifting completely off before anything could happen.  
  
"Again?!" Dean asked, anger boiling.  
  
"Think of this as," he paused, getting off the bed so he could stare at the naked man before him. "Payback. For making me stand outside your door while you and whomever you brought home that night, listening to everything going on,"   
  
Castiel wasn't upset. He really can't be. At the time he had wished it was him during those moments. Instead, he had to stand outside the door, per Dean’s commands, and battle a raging hard-on every time.  
  
"What the hell?" Dean asked in exasperation.

"You wanted this, and I am _very_ happy you made the first move. And since I have you now, _all_ to myself, I'm gonna make you feel how I did during those moments," Castiels smile widened at the equal part lust and horror as he pulled his pants on.  
  
"...wish you'd let me know sooner. But uh-Cas, are you going to untie me?” Dean asked, tugging at his restraints.   
  
Castiel turned towards the man, a finger on his chin as he contemplated the idea.  
  
“Nah, I want you to take a break and then we can pick up again until we get to 5th base.”  
  
“Wha-there’s no such thing!” Dean all but shouted as he watched the man walking closer to the door.  
  
Grabbing the doorknob, Castiel turned back with a smile on his face.  
  
“You poor sheltered boy,” before turning the handle, opening the door and walking out.


End file.
